methyl (2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanoate

• ChemBase ID: 177124
• Molecular Formular: C15H15N3O3
• Molecular Mass: 285.2979
• Monoisotopic Mass: 285.11134136
• SMILES: c1ncc(nc1)C(=O)N[C@H](C(=O)OC)Cc1ccccc1
• Canonical SMILES: COC(=O)[C@@H](NC(=O)c1nccnc1)Cc1ccccc1
• InChI: InChI=1S/C15H15N3O3/c1-21-15(20)12(9-11-5-3-2-4-6-11)18-14(19)13-10-16-7-8-17-13/h2-8,10,12H,9H2,1H3,(H,18,19)/t12-/m0/s1
• InChIKey: AGZXSMPTQAISJW-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanoate
• IUPAC Traditional name: methyl (2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanoate
• Synonyms: N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester; 3-Phenyl-2-[(pyrazine-2-carbonyl)amino]propionic Acid Methyl Ester; N-Pyrazinylcarbonyl-L-phenylalanine Methyl Ester

Database IDs

• CAS Number: 73058-37-4
• PubChem SID: 164233034
• PubChem CID: 12580944

CALCULATED PROPERTIES

• Acid pKa: 13.551726
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.84703535
• LogD (pH = 7.4): 0.84703535
• Log P: 0.84703565
• Molar Refractivity: 75.3139 cm^3
• Polarizability: 29.128368 Å^3
• Polar Surface Area: 81.18 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Ethanol
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - P841510

Used for the synthesis of Bortezomib from L-phenylalanine via dipeptidyl boronic acid ester intermediates.

REFERENCES

• Zhu, Y., et al.: J. Med. Chem., 52, 4192 (2009)